Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2021-09-20 DOI:10.1007/s10847-021-01108-z

Mika Sawai, Sayaka Matsumoto, Yuki Mimura, Yoshitane Imai, Shoko Yamazaki, Nobuko Kanehisa, Norimitsu Tohnai, Eiji Nakata, Hiroshi Takashima

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引用次数: 1

Abstract

Circularly polarized luminescence (CPL) organic dyes are currently receiving a great interest, but there are still not many reported observations of CPL spectra of hydrophobic dyes from aqueous solution. We have prepared hydrophobic pyrene derivatives and dissolved them into aqueous solutions with γ-cyclodextrin (γ-CD) by using grinding technique. Among these derivatives, (pyrene-1-carbonyl)serine (PySer) forms a spatially restricted dimer in the hydrophobic chiral cavity of γ-CD and exhibits excimer emission with a high quantum yield of Φ_f = 0.68. In addition, circular dichroism and CPL signals were induced for the complex. The strong g_CPL value of g_CPL = + 2.2 × 10⁻³ was obtained, which may be attributed to the interaction between the hydroxyl groups in the side chain of PySer with those of γ-CD and it strengthens the chiral dimeric structure.

Graphic abstract

Abstract Image

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研磨溶解水溶液中疏水性芘衍生物/γ-环糊精(γ-CD)配合物的圆偏振发光特性

圆偏振发光(CPL)有机染料是目前研究的热点，但对疏水染料的CPL光谱的研究还不多见。制备了疏水性芘衍生物，并采用研磨法将其与γ-环糊精(γ-CD)溶解在水溶液中。在这些衍生物中，(芘-1-羰基)丝氨酸(PySer)在γ-CD的疏水手性腔中形成空间受限二聚体，并具有高量子产率Φf = 0.68的准分子发射。此外，该复合物还诱导出圆二色性和CPL信号。得到gCPL = + 2.2 × 10−3的强gCPL值，这可能是由于PySer侧链上的羟基与γ-CD的羟基相互作用，增强了手性二聚体结构。图形抽象

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来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry Agricultural and Biological Sciences-Food Science

CiteScore

4.10

自引率

8.70%

发文量

期刊介绍： The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.